NZ556761A - Substituted arylamine compounds and their use as 5-HT6 modulators - Google Patents
Substituted arylamine compounds and their use as 5-HT6 modulatorsInfo
- Publication number
- NZ556761A NZ556761A NZ556761A NZ55676106A NZ556761A NZ 556761 A NZ556761 A NZ 556761A NZ 556761 A NZ556761 A NZ 556761A NZ 55676106 A NZ55676106 A NZ 55676106A NZ 556761 A NZ556761 A NZ 556761A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- phenyl
- alkyl
- piperazin
- mmol
- Prior art date
Links
- -1 arylamine compounds Chemical class 0.000 title claims abstract description 104
- 150000001875 compounds Chemical class 0.000 claims abstract description 347
- 239000003814 drug Substances 0.000 claims abstract description 50
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 154
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 125
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 63
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 56
- 208000035475 disorder Diseases 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 201000000980 schizophrenia Diseases 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 34
- 208000008589 Obesity Diseases 0.000 claims description 30
- 235000020824 obesity Nutrition 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 230000000694 effects Effects 0.000 claims description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 27
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 150000007942 carboxylates Chemical class 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 208000010877 cognitive disease Diseases 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 108091005435 5-HT6 receptors Proteins 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 102100040368 5-hydroxytryptamine receptor 6 Human genes 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 101710150235 5-hydroxytryptamine receptor 6 Proteins 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 15
- 125000004442 acylamino group Chemical group 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 15
- 239000010452 phosphate Substances 0.000 claims description 15
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 15
- 208000028698 Cognitive impairment Diseases 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 14
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 14
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 14
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 14
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 14
- 150000003467 sulfuric acid derivatives Chemical group 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 208000010643 digestive system disease Diseases 0.000 claims description 11
- 150000002430 hydrocarbons Chemical group 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 208000023105 Huntington disease Diseases 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 125000004437 phosphorous atom Chemical group 0.000 claims description 10
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- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 208000028017 Psychotic disease Diseases 0.000 claims description 9
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 208000019906 panic disease Diseases 0.000 claims description 9
- 239000004031 partial agonist Substances 0.000 claims description 9
- LCOFMNJNNXWKOC-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-4-amine Chemical compound C1=CC=C2C(N)CCOC2=C1 LCOFMNJNNXWKOC-UHFFFAOYSA-N 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
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- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 8
- 206010047700 Vomiting Diseases 0.000 claims description 8
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 8
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- 208000011117 substance-related disease Diseases 0.000 claims description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
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- 208000019695 Migraine disease Diseases 0.000 claims description 7
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- 208000032841 Bulimia Diseases 0.000 claims description 6
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 6
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 4
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- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 4
- SPGRIJRGBVPWLZ-UHFFFAOYSA-N 1-benzothiophen-3-amine Chemical compound C1=CC=C2C(N)=CSC2=C1 SPGRIJRGBVPWLZ-UHFFFAOYSA-N 0.000 claims description 3
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- ZILHMCBPNNUFLP-UHFFFAOYSA-N 3-[1-(5-fluoro-2-methoxy-3-methylphenyl)ethyl]-2-methylsulfonyl-5-piperazin-1-ylaniline Chemical compound COC1=C(C)C=C(F)C=C1C(C)C1=CC(N2CCNCC2)=CC(N)=C1S(C)(=O)=O ZILHMCBPNNUFLP-UHFFFAOYSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
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- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
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- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
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- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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EP (1) | EP1856075A1 (ja) |
JP (2) | JP5186219B2 (ja) |
KR (1) | KR20070097590A (ja) |
AU (1) | AU2006209216A1 (ja) |
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NO (1) | NO20074324L (ja) |
NZ (1) | NZ556761A (ja) |
RU (1) | RU2440996C2 (ja) |
WO (1) | WO2006081332A1 (ja) |
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- 2006-01-25 BR BRPI0606110-9A patent/BRPI0606110A2/pt not_active IP Right Cessation
- 2006-01-25 NZ NZ556761A patent/NZ556761A/en not_active IP Right Cessation
- 2006-01-25 AU AU2006209216A patent/AU2006209216A1/en not_active Abandoned
- 2006-01-25 CA CA2595607A patent/CA2595607C/en not_active Expired - Fee Related
- 2006-01-25 MX MX2007008279A patent/MX2007008279A/es active IP Right Grant
- 2006-01-25 JP JP2007552407A patent/JP5186219B2/ja not_active Expired - Fee Related
- 2006-01-25 EP EP06719542A patent/EP1856075A1/en not_active Withdrawn
-
2007
- 2007-07-18 IL IL184705A patent/IL184705A0/en unknown
- 2007-08-07 MA MA30129A patent/MA29429B1/fr unknown
- 2007-08-24 NO NO20074324A patent/NO20074324L/no not_active Application Discontinuation
-
2011
- 2011-05-10 US US13/104,450 patent/US8604021B2/en not_active Expired - Fee Related
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2012
- 2012-03-16 JP JP2012060984A patent/JP2012111784A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2006081332A1 (en) | 2006-08-03 |
CA2595607A1 (en) | 2006-08-03 |
US8604021B2 (en) | 2013-12-10 |
US20060205737A1 (en) | 2006-09-14 |
CA2595607C (en) | 2014-07-15 |
MX2007008279A (es) | 2008-02-15 |
RU2440996C2 (ru) | 2012-01-27 |
JP2012111784A (ja) | 2012-06-14 |
BRPI0606110A2 (pt) | 2009-06-02 |
AU2006209216A1 (en) | 2006-08-03 |
US7968538B2 (en) | 2011-06-28 |
KR20070097590A (ko) | 2007-10-04 |
US20120115850A1 (en) | 2012-05-10 |
EP1856075A1 (en) | 2007-11-21 |
JP5186219B2 (ja) | 2013-04-17 |
IL184705A0 (en) | 2007-12-03 |
RU2007132161A (ru) | 2009-03-10 |
NO20074324L (no) | 2007-10-25 |
JP2008528517A (ja) | 2008-07-31 |
MA29429B1 (fr) | 2008-05-02 |
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